54784-38-2Relevant academic research and scientific papers
Dichloroiodoisocyanuric acid: A new reagent for regioselective coiodination of alkenes and iodination of activated arenes
Da Silva Ribeiro, Rodrigo,Esteves, Pierre M.,De Mattos, Marcio C.S.
experimental part, p. 228 - 235 (2012/05/05)
Dichloroiodoisocyanuric acid was prepared in 93% by heating trichloroisocyanuric acid with 1.05 mol equiv. of iodine. This new reagent is very efficient for regioselective electrophilic iodination of activated arenes. Alkenes react with dichloroiodoisocyanuric acid in the presence of oxygenated nucleophiles (water, alcohols, and acetic acid), leading to the corresponding iodohydrins, β-iodoethers and β-iodoacetates with reaction times of less than one minute and with a high degree of regioselectivity. Enol ethers resulted in the regioselective formation of the corresponding iodine-dialkylacetals. Experimental results and DFT calculations showed that dichoroiodoisocyanuric acid is more reactive with unsaturated systems than triiodoisocyanuric acid.
Triiodoisocyanuric acid: a new and convenient reagent for regioselective coiodination of alkenes and enolethers with oxygenated nucleophiles
Ribeiro, Rodrigo da S.,Esteves, Pierre M.,de Mattos, Marcio C.S.
, p. 8747 - 8751 (2008/03/18)
The reaction of triiodoisocyanuric acid (prepared from I2 and trichloroisocyanuric acid in 90% yield) with alkenes in the presence of oxygenated nucleophilic solvents (alcohols, AcOH and H2O) led to the corresponding β-iodoethers, β-iodoacetates and iodohydrins, in 66-98% isolated yield. Enolethers reacted with triiodoisocyanuric acid in MeOH to produce dialkylacetals (70-83%).
N-iodosaccharin - A new reagent for iodination of alkenes and activated aromatics
Dolenc, Darko
, p. 544 - 546 (2007/10/03)
A mild and efficient iodination reagent, N-iodosaccharin was prepared. Iodination of activated aromatics and alkenes with the reagent takes place fast and under very mild conditions, without the aid of strong acids or heavy metals. The reagent does not affect oxidizable groups, such as hydroxyl or aldehyde.
Iodohydrins: An easy route to epoxides from alkenes
Sanseverino, Antonio Manzolillo,De Mattos, Marcio C. S.
, p. 559 - 572 (2007/10/03)
The preparation of epoxides is efficiently achieved by reaction of alkenes with I2 in aqueous dioxane in the presence of Cu(OAc)2.H2O followed by treatment with KOH in a biphasic system (H2O/ether/pentane).
An improved synthesis of β-iodo ethers and iodohydrins from alkenes
Sanseverino, Antonio M.,De Mattos, Marcio C. S.
, p. 1584 - 1586 (2007/10/03)
The preparation of diverse β-iodo ethers and iodohydrins is efficiently achieved in mild conditions by reaction of alkenes with two equivalents of I2 and alcohols (EtOH, i-PrOH, t-BuOH) or water, respectively.
A New Synthesis of trans-Iodohydrins using Iodine-Cerium(IV) Salts
Horiuchi, C. Akira,Ikeda, Akira,Kanamori, Miyuki,Hosokawa, Haruomi,Sugiyama, Takashi,Takahashi, T. Tomoyoshi
, p. 60 - 61 (2007/10/03)
The reaction of cycloalkene with iodine-cerium(IV) ammonium nitrate (CAN) in acetonitrile-water (10:1-1:1) affords the corresponding trans-iodohydrins and trans-iodonitrates; when iodine-cerium(IV) sulfate (CS) in acetonitrile-water (10:1) at 50 deg C is used, trans-iodohydrins are obtained preferentially.
Regio- and Stereoselective Synthesis of β-Halohydrins from 1,2-Epoxides with Ammonium Halides in the Presence of Metal Salts
Chini, Marco,Crotti, Paolo,Gardelli, Cristina,Macchia, Franco
, p. 3805 - 3812 (2007/10/02)
A simple efficient, stereoselective, and regioselective method for the synthesis of β-chlorohydrins, β-bromohydrins, and β-iodohydrins by the direct opening of 1,2-epoxides with the corresponding ammonium halide in acetonitrile, in the presence of metal salts, is described.This new method appears to be of general use and competitive with the other methods previously reported.
Use of Polymeric Phosphine-Halogen Complexes in the Conversion of Epoxides to Halohydrins
Caputo, Romualdo,Ferreri, Carla,Noviello, Silvana,Palumbo, Giovanni
, p. 499 - 501 (2007/10/02)
Polystyryldiphenylphosphine-halogen complexes are convenient reagents for converting epoxides to halohydrins under mild and non-acidic conditions.The method requires only a filtration and evaporation process for product isolation.
A NEW GENERAL SYNTHESIS OF HALOHYDRINS
Palumbo, Giovanni,Ferreri, Carla,Caputo, Romualdo
, p. 1307 - 1310 (2007/10/02)
A new synthetic method has been devised for the rapid conversion of epoxides to chloro-, bromo- and iodo-hydrins in quantitative yield, under mild conditions and in the absence of protic acids.
